EP0326959B1 - Perfume base composition comprising 2-cyclohexylpropanal and process for the preparation of this compound - Google Patents

Perfume base composition comprising 2-cyclohexylpropanal and process for the preparation of this compound Download PDF

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Publication number
EP0326959B1
EP0326959B1 EP89101439A EP89101439A EP0326959B1 EP 0326959 B1 EP0326959 B1 EP 0326959B1 EP 89101439 A EP89101439 A EP 89101439A EP 89101439 A EP89101439 A EP 89101439A EP 0326959 B1 EP0326959 B1 EP 0326959B1
Authority
EP
European Patent Office
Prior art keywords
cyclohexylpropanal
perfume base
base composition
compound
preparation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP89101439A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0326959A3 (en
EP0326959A2 (en
Inventor
Junji Koshino
Yoshiaki Fujikura
Manabu Fujita
Nao Toi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kao Corp
Original Assignee
Kao Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Kao Corp filed Critical Kao Corp
Publication of EP0326959A2 publication Critical patent/EP0326959A2/en
Publication of EP0326959A3 publication Critical patent/EP0326959A3/en
Application granted granted Critical
Publication of EP0326959B1 publication Critical patent/EP0326959B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/002—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by dehydrogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
    • C07C47/105—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing rings
    • C07C47/11—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing rings monocyclic

Definitions

  • This invention relates to a perfume base composition, and more specifically to a perfume base composition containing 2-cyclohexylpropanal and having no allergic effects.
  • Japanese Patent Application Laid-Open No. 204115/1984 discloses that the following compounds: give off fresh green fragrance and are excellent as perfume bases for soaps, detergents and cosmetics. According to the above patent publication, the above compounds are said to be obtained as an about 2:8 mixture by an oxo reaction among 4-vinylcyclohexene-1, carbon monoxide and hydrogen.
  • the perfume base composition according to the present invention comprises 2-cyclohexylpropanal.
  • 2-Cyclohexylpropanal can be prepared, for example, by the following process (A) described in J. Org. Chem., 32 , 113 (1967): or by the following process (B) disclosed in J. Org. Chem., 43 , 3792 (1978): These processes are however not considered to be industrial processes from the viewpoint of the number of reaction steps and the yield of the final compound.
  • a perfume base composition as defined in claim 1 which comprises 2-cyclohexylpropanal.
  • the present inventors hence contemplated of obtaining the target compound by oxidising 2-hexylpropanol which is industrially available with industrial standpoint, an investigation has been conducted on liquid-phase dehydrogenation having such merits that no special equipment is required and waste materials are not very troublesome.
  • conversions as low as about 30-35% are only available in conventional liquid-phase dehydrogenation reactions, a conversion as high as 67% is achieved in the case of the compound according to this invention and its selectivity is as high as 91%.
  • a novel preparation process for the compound useful in the novel perfume base composition namely, a process for the preparation of 2-cyclohexylpropanal, which comprises subjecting 2-cyclohexylpropanol to liquid-phase dehydrogenation.
  • the present invention has made it possible to prepare 2-cyclohexylpropanol advantageously on an industrial scale.
  • the perfume base composition according to this invention can impart sweet, rich and pleasant fragance to formulated perfume bases owing to the fresh-citrus-green-like fragance of 2-cyclohexylpropanal and are also useful as a perfume base for soaps, detergents, cosmetics and the like.
  • the process of this invention can be practised by heating 2-cyclohexylpropanol in the presence of a dehydrogenation catalyst in a solvent.
  • Illustrative examples of the dehydrogenation catalyst may include copper, silver, zinc, copper-zinc, copper-chromium, and the like.
  • the catalyst may be used in a proportion of 0.001-10 wt.% based on 2-cyclohexylpropanol.
  • Liquid paraffin is preferred as the solvent. It is preferable to use liquid paraffin in an amount of 10-500 times the weight of the catalyst.
  • the reaction may be conducted by suspending the dehydrogenation catalyst in the solvent and then feeding 2-cyclohexylpropanol continuously while distilling out the reaction product or adding 2-cyclohexylpropanol batchwise.
  • the reaction pressure may be either normal pressure or reduced pressure.
  • 2-cyclohexylpropanal Upon purification of the reaction mixture by distillation subsequent to the reaction, 2-cyclohexylpropanal can be easily obtained with high purity. 2-Cyclohexylpropanol which is also recovered by the distillation can be used again as the starting material.
  • 2-Cylohexylpropanal according to this invention can be used as a safe perfume base free of cutaneous allergic effects in soaps, detergents, cosmetics, etc.
  • the perfume base composition according to this invention may be formulated preferably by incorporating 2-cyclohexylpropanal to a content of about 0.01-10 wt.% of the whole composition.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Cosmetics (AREA)
  • Fats And Perfumes (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP89101439A 1988-01-28 1989-01-27 Perfume base composition comprising 2-cyclohexylpropanal and process for the preparation of this compound Expired - Lifetime EP0326959B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP63018387A JPH0751713B2 (ja) 1988-01-28 1988-01-28 香料組成物
JP18387/88 1988-01-28

Publications (3)

Publication Number Publication Date
EP0326959A2 EP0326959A2 (en) 1989-08-09
EP0326959A3 EP0326959A3 (en) 1990-02-07
EP0326959B1 true EP0326959B1 (en) 1994-03-30

Family

ID=11970304

Family Applications (1)

Application Number Title Priority Date Filing Date
EP89101439A Expired - Lifetime EP0326959B1 (en) 1988-01-28 1989-01-27 Perfume base composition comprising 2-cyclohexylpropanal and process for the preparation of this compound

Country Status (4)

Country Link
US (1) US4918052A (ja)
EP (1) EP0326959B1 (ja)
JP (1) JPH0751713B2 (ja)
DE (1) DE68914175T2 (ja)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0749593B2 (ja) * 1989-07-28 1995-05-31 花王株式会社 ２―シクロヘキシルプロピオン酸またはその誘導体を含有する調合香料組成物
EP1029845A1 (en) * 1999-02-15 2000-08-23 Quest International B.V. 2-(4-Tert-pentylcyclohexyl)acetaldehyde and its use as fragrance compound
ES2226644T3 (es) * 1999-05-19 2005-04-01 Firmenich S.A. Utilizacion de acetaldehidos sustituidos que tienen un sustituyente ciclico como ingredientes perfumantes.
US6172016B1 (en) * 1999-07-12 2001-01-09 Bush Boakes Allen Inc. Fragrance materials
GB2389856A (en) * 2002-06-18 2003-12-24 Reckitt Benckiser Nv Removal of stains from plastics

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB191221367A (en) * 1912-09-19 1913-09-19 James Yate Johnson Improvements in the Manufacture of Aldehydes and Ketones from the Corresponding Alcohols.
US2746993A (en) * 1949-12-16 1956-05-22 Ici Ltd Dehydrogenation of alcohols
US2710825A (en) * 1954-04-16 1955-06-14 Fmc Corp Perfume composition
US3940446A (en) * 1971-07-08 1976-02-24 Universal Oil Products Company Dehydrogenation of alcohols
US4036774A (en) * 1975-08-04 1977-07-19 International Flavors & Fragrances Inc. Fragrant soap compositions containing alpha-substituted acetaldehyde and ketone
GB1528528A (en) * 1976-08-09 1978-10-11 Shell Int Research Cyclohexane derivatives
EP0092031B1 (fr) * 1982-04-15 1984-12-27 Firmenich Sa 1(7)-p-Menthène-9-al et son utilisation en tant qu'ingrédient parfumant et aromatisant
JPS59204115A (ja) * 1983-05-04 1984-11-19 Kao Corp 香料組成物

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
J. Org. Chem, 32, 113 (1967) *

Also Published As

Publication number Publication date
DE68914175T2 (de) 1994-11-10
JPH0751713B2 (ja) 1995-06-05
US4918052A (en) 1990-04-17
EP0326959A3 (en) 1990-02-07
DE68914175D1 (de) 1994-05-05
EP0326959A2 (en) 1989-08-09
JPH01193238A (ja) 1989-08-03

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